Who’s the coolest person (other than a family member) you’ve ever sat near on an airplane?  Up until a couple weeks ago, Brent Jackson, President of BreakFront, would have likely had to rack his brain for a decent response; but a recent trip from Omaha, NE to Charlotte, NC changed things a bit.

Ben SteinSneakers and suits

Brent, a frequent flier as of late, got upgraded to “first class” on a small plane (you know…the ones with two seats on one side and one seat on the other) and was seated near a man who was heading from Sioux City, IA (where he spoke at a conference) to Greenville, SC to visit his son.  Sounds average enough, right? But as Brent got settled and took in his surroundings and peers a bit, he recognized the man seated diagonally in front of him at first glance – a familiar face combined with an unmistakable voice. And if those clues weren’t enough – a quick glance at the man’s wardrobe sealed the deal – A suit artfully paired with sneakers. Ben Stein!

I know what you’re thinking right now…so let’s just get it out of your system before we continue…

“Bueller?  Bueller?” “For dry, red eyes, Clear Eyes is awesome.  It removes redness and has an ingredient to moisturize. Wooww.”

Realizing this was probably the coolest person he had sat near on a plane thus far, Brent shamelessly snapped a paparazzi pic, (the one shown above) and relished the fact that he could now confirm that Ben Stein does, in fact, wear sneakers with a suit.

Speaking up

While striking a conversation diagonally on the plane seemed difficult, Brent found a good moment as they waited for their gate-checked bags, and was genuinely pleased to find out that Ben Stein is a down-to-earth very approachable person.  According to Brent, Stein was VERY easy to talk with (for anyone), extremely friendly and a positive person.

People are funny.  In general, many of us would get anxiety over the idea of initiating a conversation with a celebrity, a well-known person in the industry or even a stranger in general.  Many of us assume that others (especially celebrities) wouldn’t want to be bothered – a thought that even crossed Brent’s mind on the airplane.  But without risk, there can be no reward.  Brent risked getting snubbed for a once in a lifetime chance to chat with Ben Stein; and he was rewarded with a great conversation and really good insight from a pleasant family man. Ben spoke of his recent trips to places like Iowa and Sioux Falls, South Dakota – places most wouldn’t associate with positive feelings (no slam intended), but he spoke with much enthusiasm about the amazing people there and how friendly and genuine they are and how he looks forward to going again.

The moral of this story? Pushing boundaries and taking risks – whether in business or in airport conversation – can be way worth your while.  When you stop letting assumptions rule your actions, you’ll learn things, have meaningful conversations, and life will be more interesting.  Sure, sometimes things won’t go as planned, but often they’ll exceed your expectations.